Water → Benzoic acid, 4-iodo-2-methoxy-, methyl ester

HRID 861785

Reaction equation

HRID 861785 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].I[CH3:16].O>CN(C=O)C>[I:14][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:3][CH3:16])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 22619468Benzoic acid, 4-iodo-2-methoxy-, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

238 mg (7.9 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 2 g (7.2 mmol) of methyl 2-hydroxy-4-iodobenzoate in 50 ml of DMF was added dropwise and stirring was carried out until gas evolution had ceased. 540 μl (8.6 mmol) of iodomethane were then added and stirring was carried out at room temperature for two hours. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. 2.1 g (100%) of methyl 4-iodo-2-methoxybenzoate were recovered.

Workup

  1. stirringstirring
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. custom2.1 g (100%) of methyl 4-iodo-2-methoxybenzoate were recovered

Sources & evidence

ORD record
ord-753be02e07084d23862382f5394502aa
Source dataset
uspto-grants-1998_02
Patent number
US05716624

Linked notes

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